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Synlett 1993; 1993(3): 177-185
DOI: 10.1055/s-1993-22393
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Ring Opening Reactions of Oxabicyclic Compounds as a Route to Cyclic and Acyclic Compounds with Multiple Stereocenters

Mark Lautens*
  • *Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 1A1
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Publication Date:
19 March 2002 (online)

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The ring opening of oxabicyclic compounds with a variety of nucleophiles can serve as a useful reaction for the synthesis of cyclic and acyclic compounds with multiple stereocenters. Highly regio- and stereoselective reactions have been observed with organocuprates, silylcuprates, organolithium reagents and organomagnesium compounds. 1. Introduction 2. Research Plan and Related Literature Information 3. Organocuprate Openings 4. Organolithium Openings of Oxabicyclo[3.2.1] Systems 5. Oxidative Cleavage of the Ring 6. Rifamycin S Subunit and the endo Alkoxy Effect 7. Regioselective Ring Openings 8. Reductive Ring Openings, Synthesis of a Subunit of Ionomycin 9. Reactivity of Silyl Nucleophiles 10. Conclusions and Future Studies